5-propylaminocamptothecin

ID: ALA219664

PubChem CID: 44420361

Max Phase: Preclinical

Molecular Formula: C23H23N3O4

Molecular Weight: 405.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5-Propylaminocamptothecin | 5-propylaminocamptothecin|CHEMBL219664

Canonical SMILES:  CCCNc1c2c(c(=O)n3c1-c1nc4ccccc4cc1C3)COC(=O)[C@]2(O)CC

Standard InChI:  InChI=1S/C23H23N3O4/c1-3-9-24-19-17-15(12-30-22(28)23(17,29)4-2)21(27)26-11-14-10-13-7-5-6-8-16(13)25-18(14)20(19)26/h5-8,10,24,29H,3-4,9,11-12H2,1-2H3/t23-/m0/s1

Standard InChI Key:  MKWUHPUDFRAUAT-QHCPKHFHSA-N

Molfile:  

     RDKit          2D

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   -4.9200  -11.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2429  -11.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2446  -10.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5670  -10.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663  -11.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8887  -11.7538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941  -10.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2160  -10.5748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2160  -10.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5014  -10.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5027  -11.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2224  -11.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9412  -11.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9359  -10.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156  -10.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036  -12.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6354  -12.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439  -13.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630  -11.7603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -9.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180  -12.5971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9361  -13.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533  -12.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3714  -13.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
 14 17  1  0
  6  7  1  0
 16 15  1  0
 15 12  1  0
  7 10  2  0
  1  2  2  0
 16 17  2  0
  9  8  2  0
 17 18  1  0
  8  5  1  0
 18 19  1  0
  9 10  1  0
 19 20  1  0
  5  4  2  0
 20 21  1  0
 21 16  1  0
  4  1  1  0
 18 22  1  1
 18 23  1  0
 10 13  1  0
 23 24  1  0
 12 11  1  0
 19 25  2  0
 11  9  1  0
 15 26  2  0
  2  3  1  0
 14 27  1  0
  5  6  1  0
 27 28  1  0
 12 13  1  0
 28 29  1  0
  3  6  2  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA219664

   5-Propylaminocamptothecin

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 405.45

Molecular Weight (Monoisotopic): 405.1689

AlogP: 2.90

#Rotatable Bonds: 4

Polar Surface Area: 93.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.64

CX Basic pKa: 1.80

CX LogP: 1.50

CX LogD: 1.50

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: 0.29

References

1. Torregrossa J, Bubley GJ, Jones GB..  (2006)  Microwave expedited synthesis of 5-aminocamptothecin analogs: Inhibitors of hypoxia inducible factor HIF-1alpha.,  16  (23): [PMID:16971123] [10.1016/j.bmcl.2006.08.103]

Source

Source(1):

• Scientific Literature